Higher education (HE) is required to educate educational experts who can design teaching and learning processes, which trigger students’ interest, motivate and engage them. Although research has shown the importance of triggers, particularly in challenging situations, academics still lack practical and theoretical examples on how to design inspiring learning experiences. In addition, little is known about the connection of drama, gamification and engagement in HE learning processes in outdoor contexts. The aim in this chapter is two-fold. First, we describe a gamified role-play design, which was implemented in higher education studies, in an international master’s degree program in the forest, and the students studied three concepts—engagement, gamification and collaboration—both by reading scientific articles and through their collaborative experiences in the forest. Second, to analyse students’ engagement in the gamified activities, and see which elements positively trigger their interest and engagement in the activities and which on the other hand negatively affect their interest. The data obtained comprises students’ self-evaluations throughout the activities and their reflections after the course were considered. The results show that the most important triggers are: (1) collaboration and learning together; (2) role-play activity itself, particularly when it is novel and provides feelings of success; and (3) outdoors activity. Other-directed and intellectual-creative playful triggers were the most evident. Frustration and anxiety can weaken engagement. Implications for educators are discussed.